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Born John Jervis Halliday, he was the son of Admiral John Richard Delap Halliday (who in 1821 assumed by Royal license the surname and arms of Tollemache in lieu of Halliday), eldest son of Lady Jane Halliday, youngest daughter and co-heir of Lionel Tollemache, 4th Earl of Dysart. His mother was Lady Elizabeth Stratford, daughter of John Stratford, 3rd Earl of Aldborough.

Little is known of his education and it is thought that he received a private education which did not lead to university. He inherited considerable wealth, including Helmingham Hall in Suffolk and estates in Northamptonshire, Cheshire and Ireland.[1]

Lord Tollemache married Georgina Louisa Best, daughter of Thomas Best, in 1826; they had five children together. After her death in 1846, he married Eliza Georgiana Duff, daughter of Sir James Duff, in 1850; they had nine children together.

Lord Tollemache died in December 1890, aged 85, and was succeeded in the barony by his eldest son from his first marriage, Wilbraham Frederic Tollemache. The eldest son from his second marriage, the Hon. John. R. D. Tollemache, married Eleanor Starnes, the daughter of Hon. Henry Starnes and his wife, Eleanor Stuart.[3]

Lady Tollemache, who was 24 years younger than her husband, died in 1918.[2]

Tollemache was the largest landowner in Cheshire, owning 28,651 acres (115.95 km2). His estate exceeded those of the Duke of Westminster who owned 15,138 acres (61.26 km2), Lord Crewe with 10,148 acres (41.07 km2) and Lord Cholmondeley with 16,992 acres (68.76 km2). He was considered to be a good estate manager; William Ewart Gladstone described him as "the greatest estate manager of his day". He was generous to his tenants and advocated improvement of their social conditions. He believed in a self-reliant labouring class and made popular the idea of his tenants having a cottage with sufficient land to keep a few animals. His catch-phrase for this was "three acres and a cow", a policy he carried out in Framsden, the estate village of Helmingham Hall. In addition to building many cottages with land attached he built over 50 farmhouses. On this project he spent £280,000.[1]

Tollemache's major building project was a family home in the form of a Norman-style castle, Peckforton Castle, on a massive scale on Peckforton Hills in his Cheshire estate. It cost around £60,000 (£5,600,000 as of 2015),[4][5] and is described as the last serious fortified home built in England.[6]